Benzene → HCID 13937603, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[O:10][N:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH:20]1[CH:25]=CC=C[CH:21]=1>>[CH:20]([O:14][C:13]([CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:12]1)=[O:15])([CH3:25])[CH3:21]Participants
Procedure
3-(4-chlorophenyl)-2-isoxazoline-5-carboxylic acid (2.2 g) prepared in Synthesis Example 3 was added with 20 ml of benzene and 1.4 g of thionyl chloride. After refluxing for 30 minutes, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in 20 ml of toluene and added with 0.7 g of isopropyl alcohol. The mixture was further added with 0.8 g of pyridine at 0° to 10° C. and reacted for an hour at the room temperature. The reaction mixture was washed with a dilute aqueous hydrochloric acid solution and successively with water. The resulting solution was concentrated under reduced pressure and then purified by silica gel column chromatography (eluent; toluene) to give 2.0 g (75% yield) of oily desired product.
Workup
- temperatureAfter refluxing for 30 minutes
- concentrationthe reaction mixture was concentrated under reduced pressure
- dissolutionThe resulting residue was dissolved in 20 ml of toluene
- additionadded with 0.7 g of isopropyl alcohol
- additionThe mixture was further added with 0.8 g of pyridine at 0° to 10° C.
- customreacted for an hour at the room temperature
- washThe reaction mixture was washed with a dilute aqueous hydrochloric acid solution and successively with water
- concentrationThe resulting solution was concentrated under reduced pressure
- custompurified by silica gel column chromatography (eluent; toluene)
Sources & evidence
- ORD record
- ord-a5b22d48d85d475c9e2870a540982f6a
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889551
Reaction notes
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